105 Rolling Way, Peekskill, NY 10566
Property image
Property image
OFF MARKET

$396,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,480 sqft

105 Rolling Way, Peekskill, NY 10566

Est. Refi. Payment $2,598/mo*
Refinance Your Home
Currently Off Market - Sold Jan 8, 2016 for $170,000

Home Value

Trulia Estimate
$397K
Since last month
Increased$9K (+2.4%)
Since last year
Increased$28K (+7.6%)
Since last sale
Increased$226K (+133.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +134% in the last 10 years
MonthEstimated value
2026
August 2026$396K
July 2026$387K
June 2026$388K
May 2026$375K
April 2026$363K
March 2026$368K
February 2026$355K
January 2026$351K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.46
Single-Family Home
$200,000
04/23/26
3
1
1,168
0.27
Single-Family Home
$400,000
01/29/26
2
1.5
1,240
0.18
Single-Family Home
$275,000
02/09/26
3
1
1,200
0.62
Single-Family Home
$360,000
10/24/25
2
2
1,681
0.23
Single-Family Home
$350,000
01/09/26
3
1
1,200
0.37
Single-Family Home
$585,000
03/04/26
3
2
1,770
0.29
Single-Family Home
$559,000
05/22/26
3
2
1,248
0.57
Single-Family Home
$505,500
09/30/25
2
2
1,700
0.72
Single-Family Home
$310,000
11/14/25
3
2
1,850
0.35
Single-Family Home
$360,000
12/31/25
3
1
1,008

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0.03
$455,500
3
1.5
2,100
Off Market
0.07
$425,700
3
1.5
1,470
Off Market
0.01
$456,000
3
1.5
1,440
Off Market
0.01
$389,200
3
1.5
1,400
Off Market
0.08
$422,300
3
1.5
1,480
Off Market
0.02
$312,100
3
1.5
1,450
Foreclosure
0.09
$212,500
1
1
750
Recently Sold
0.05
$266,400
2
1
900
Off Market
0.10
$290,000
2
1
900
Recently Sold
0.10
$229,000
1
1
750
Recently Sold
0.11
$227,500
1
1
750
Off Market
0.07
$495,200
3
1.5
2,280
Off Market

Local Information

  • Map ViewExplore the area around 105 Rolling Way.
  • Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Living Area
1,480 sqft
Price/Sqft
$268

About this House

Move right in to this spacious three bedroom town house in Historic Peekskill. This freshly painted condo has plenty of closet space, a private backyard space for your enjoyment. Pool/ Playground and clubhouse included. No additional fee for use. Enjoy all that Peekskill has to offer. Minutes to Metro North Peekskill train station. Just 1 Hr. to GCS. Close to all shopping, transportation , Trendy restaurants, Paramount theater, coffee shops and much more . Credit score of 650+ and background check. 1st months rent plus security . No Pets / No smoking .
105 Rolling Way, Peekskill, NY 10566 is a 3 bedroom, 2 bathroom, 1,480 sqft single-family home built in 1965. It last sold for $170,000 on Jan 8, 2016. More recently, it was listed as a rental in December 2019 with an asking price of $2,300 per month. That rental listing was removed on February 7, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $396,800, with a rent estimate of $3,676/month.

Home Details for 105 Rolling Way

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Exterior: Vinyl, Brick

Community

Units in Building: 1

Lot Information

Lot Area: 2257 sqft

Price and Tax history

DateEventPrice
Feb 7, 2020
Source: Agent Provided
ListingRemoved
$2,300
Dec 12, 2019
Source: Agent Provided
Listed For Rent
$2,300
Mar 7, 2016
Source: Agent Provided
ListingRemoved
$2,000
Jan 19, 2016
Source: Agent Provided
Listed For Rent
$2,000
Jan 8, 2016
Source: OneKeyยฎ MLS as distributed by MLS GRID #H4529646
Sold
$170,000

Market trends in Peekskill

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
โ€”
Sale-to-List Price
โ€”
Price per sq ft
โ€”
Available listings
70
8
MoM

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Peekskill

At least 317 Trulia users voted on each feature.
  • 81 % Say it's dog friendly

  • 78 % Say there are sidewalks

  • 76 % Say car is needed

  • 73 % Say it's walkable to restaurants

  • 72 % Say there's holiday spirit

  • 71 % Say yards are well-kept

  • 68 % Say parking is easy

  • 66 % Say it's walkable to grocery stores

  • 66 % Say kids play outside

  • 63 % Say people would walk alone at night

  • 61 % Say streets are well-lit

  • 59 % Say neighbors are friendly

  • 58 % Say it's quiet

  • 56 % Say there's wildlife

  • 55 % Say they plan to stay for at least 5 years

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Alex Hudgins
    "Great commuter train service. Close to shopping very good neighborhood. Prices going up fast. Move in soon. "
  • Cassie01616
    "Some areas no sidewalks. Make sure parents speak up for kids in school and show support. Good sense of community. "
  • Alexandercolby
    "This neighborhood is idyllic. Wonderful diversity of cultures mixing together with appreciation of differences and and understanding of sameness. So much to do, and such a great place to raise a family. You can't beat the commute; a beautiful ride up the Hudson on the Metro-north and you're well away from the din and dirt of the city. Or if you need a little culture, you're in the heart of Manhattan in under an hour. Moving here was the best decision. "
  • Lindsay
    "Iโ€™ve lived here for 1 year. Itโ€™s a very dog friendly community and everyone speaks in the neighborhood which is very welcoming. "
  • Diann.egan1@gmail.com
    "Great dining, beautiful area parks, well maintained homes, beautiful water front, farmers markets, nice neighborhoods. "
  • Nicole P.
    "I drive, traffic isnโ€™t terrible. Summer there is less traffic on 9 to Ossining. When school is in session traffic tends to be worse."
  • Rachel S.
    "There is so much to do in this town! It has hikes, shops, amazing restaurants, and the beautiful waterfront. "
  • Alan A. S. J.
    "Itโ€™s a short drive from my apt to my job. Itโ€™s a 10 min drive or a 45 min walk of I couldnโ€™t drive for any reason"
  • Willartiles12
    "Very quite area, extremely diverse by having all sorts of different race and color. People are very friendly and helpful in Peekskill "
  • Millie P.
    "Very diverse neighborhood and local grocery stores and restaurants are within walking distance. Beautiful view by the water front and amazing sunsets. Metro north train that takes you straight into the city."
  • Nvrltgo
    "Very easy to get to the train and restaurants are amazing the ppl are nice very family friendly and helpful neighbors cab service very fast and reliable "
  • Millie P.
    "Very Diverse group of people and within walking distance to local stores. Family friendly local people and within walking distance to the water front."
  • Johnathan M.
    "The overall commute is fair but if you have a vehicle itโ€™s great. The beeline and metro north are easily accessible. Their schedules are usually spot on and rarely ever any delays. "
  • David G.
    "I lived here now for the past three years. My neighbors are extremely friendly and we all help each other out and get along with each other."
  • Mark B.
    "They do a great job with the Peekskill waterfront events and great restaurants in downtown Peekskill. "
  • Jeanee T.
    "Central location, close to everything. My job is literally a 5 minute walk or a minute drive, with a great coffee house to grab a quick cup on the way into the office "
  • Adesai
    "I use public transportation to commute to work. Number 17 express bus to white plains is only an hour and cost 2.75/trip"
  • Marie M.
    "Itโ€™s so friendly, has an art community, has character and stunning views of the best part of the Hudson River. "
  • Roxana R.
    "Itโ€™s still in good prices for rent and yes have very nice parks areas, its getting better than years ago. "
  • Mary L. C.
    "A lot of Landlords donโ€™t accept pets so itโ€™s hard to find a decent apartment that allows you to have dogs"
  • Leslie F.
    "I enjoy the diverse restaurants and activities brought by the restaurants owners. Itโ€™s a wonderful place to leave and raise a family. "
  • Leslie F.
    "Unfortunately work doesnโ€™t allow me to know what activities my community has to offer. Maybe soon Iโ€™ll look into this "
  • Ralph E.
    "keeping the focus on our prized possessions, our young. create programs that help mold the future of our country, at an early age. Nurture them, in all phases of development.. Integrate using an intelligent approach, which will allow our future to reach their maximum potential. "
  • Trulia User
    "Great community and awesome activities for family. Schools are good. Environment is safe. I will recommend Peekskill "
  • MRL
    "Tons of fun riverfront events, movies, art galleries and shows, coffeehouse music, church activities. "
  • jack
    "Great and safe neighborhood. Quiet and very respectful people. Not in all areas like that but certainly up here on mortgage hill."
  • Ashanty1025
    "iโ€™ve lived in this neighborhood for two years it good. People are really friendly around here and itโ€™s a well maintained city "
  • Alamopaula
    "The education is good for all grades and people are friendly. People look after them selfs. Most things are in walking distance from wherever you live in Peekskill. Everyone knows everyone itโ€™s a small world/town. Most busiest part of peekskill is downtown/Main Street. "
  • Sarah H.
    "very dog friendly! lots of places to take them out between dog parks and hiking trails and the riverfront "
  • Chris B.
    "block party in the center of town. Surrounded by bars and restaurants that give nightlife to this town0"

LGBTQ Local Legal Protections

Frequently asked questions about 105 Rolling Way

  • What is 105 Rolling Way estimated to be worth?
    Trulia's estimated value for 105 Rolling Way in Peekskill, NY is $396,800.
  • What is the price history for 105 Rolling Way?
    105 Rolling Way in Peekskill, NY last sold for $170,000 in January 2016.
  • Is Peekskill a buyer's or seller's market?
    Peekskill is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Peekskill?
    Residents describe Peekskill, NY as dog-friendly, pedestrian-friendly, and walkable to restaurants. See recently sold homes in Peekskill, NY.
  • Does 105 Rolling Way have air conditioning?
    Yes, 105 Rolling Way in Peekskill, NY has air conditioning.
  • How big is the lot at 105 Rolling Way?
    The lot at 105 Rolling Way in Peekskill, NY is about 0.05 acres (2,257 sq ft).

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